Water → [4-methyl-1-(propan-2-yl)-1H-imidazol-5-yl]methanol

HRID 577084Notes

Reaction equation

HRID 577084 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([CH:9]([CH3:11])[CH3:10])[C:6]=1[CH:7]=[O:8].[BH4-].[Na+].O>CO>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([CH:9]([CH3:11])[CH3:10])[C:6]=1[CH2:7][OH:8]

Participants

5

Procedure

To a 0° C. solution of 4-methyl-1-(propan-2-yl)-1H-imidazole-5-carbaldehyde (924 mg, 6.1 mmol) in anhydrous methanol (75 mL) was added sodium borohydride (425 mg, 11.2 mmol). The reaction mixture was stirred at room temperature for 3 hours. Water (20 mL) was added. Methanol was evaporated. The resultant mixture was extracted with EtOAc (1×20 mL) and 2-butanol (2×20 mL). The solution was dried over MgSO4, filtered, evaporated, and dried in vacuo, affording [4-methyl-1-(propan-2-yl)-1H-imidazol-5-yl]methanol (703 mg, 75% yield). The product was used without further purification.

Workup

  1. customMethanol was evaporated
  2. extractionThe resultant mixture was extracted with EtOAc (1×20 mL) and 2-butanol (2×20 mL)
  3. dry with materialThe solution was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-20f7fcfd8ec0480db29a3a0f46aca30d
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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